O-methyl 1-(phenylmethyl)-4-piperidineethanimidate dihydrochloride → HCID 14012846, compound

HRID 1904820Notes

Reaction equation

HRID 1904820 reaction equation
Cl.Cl.[C:3]1([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17](=[NH:20])OC)[CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH2:26][NH:27][C:28]1[C:29](N)=[CH:30][CH:31]=[CH:32][CH:33]=1>C(O)(=O)C>[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH2:26][N:27]1[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[N:20]=[C:17]1[CH2:16][CH:13]1[CH2:12][CH2:11][N:10]([CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 14518101O-methyl 1-(phenylmethyl)-4-piperidineethanimidate dihydrochlorideHCID 14518102HCID 14518102, compound

Product 1

HCID 14012846HCID 14012846, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 27.3 parts of O-methyl 1-(phenylmethyl)-4-piperidineethanimidate dihydrochloride, 14 parts of N-(2-furanylmethyl)-1,2-benzenediamine and 250 parts of acetic acid was stirred overnight at room temperature. The reaction mixture was evaporated and water was added to the residue. The whole was alkalized with sodium carbonate and extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was crystallized from 1,1'-oxybisethane. The product was filtered off and dried, yielding 15.5 parts (57%) of 1-(2-furanylmethyl)-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-benzimidazole; mp. 124.8° C. (3).

Workup

  1. customThe reaction mixture was evaporated
  2. additionwater was added to the residue
  3. extractionextracted with 4-methyl-2-pentanone
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from 1,1'-oxybisethane
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-a89994161d8b4ae4a071d7376edb07a1
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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